DE1104501B - Verfahren zur Herstellung von O, O-Dialkylthionophosphor-saeurechloriden - Google Patents
Verfahren zur Herstellung von O, O-Dialkylthionophosphor-saeurechloridenInfo
- Publication number
- DE1104501B DE1104501B DES66068A DES0066068A DE1104501B DE 1104501 B DE1104501 B DE 1104501B DE S66068 A DES66068 A DE S66068A DE S0066068 A DES0066068 A DE S0066068A DE 1104501 B DE1104501 B DE 1104501B
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- acid
- temperature
- chlorination
- phosphorus
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000002253 acid Substances 0.000 title claims description 26
- 238000000034 method Methods 0.000 title claims description 17
- 150000001805 chlorine compounds Chemical class 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 238000005660 chlorination reaction Methods 0.000 claims description 14
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 238000004821 distillation Methods 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 6
- WQYSXVGEZYESBR-UHFFFAOYSA-N thiophosphoryl chloride Chemical compound ClP(Cl)(Cl)=S WQYSXVGEZYESBR-UHFFFAOYSA-N 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- 239000012320 chlorinating reagent Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 14
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 13
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000009835 boiling Methods 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
- 229910052753 mercury Inorganic materials 0.000 description 4
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 238000004508 fractional distillation Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- -1 phosphorus halides Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009183 running Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/20—Esters of thiophosphoric acids containing P-halide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/1658—Esters of thiopolyphosphoric acids or anhydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/201—Esters of thiophosphorus acids
- C07F9/206—Esters of thiophosphorus acids containing P-halide groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US777609A US2961456A (en) | 1958-12-02 | 1958-12-02 | Preparation of thiophosphoryl compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1104501B true DE1104501B (de) | 1961-04-13 |
Family
ID=25110727
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DES66068A Pending DE1104501B (de) | 1958-12-02 | 1959-11-30 | Verfahren zur Herstellung von O, O-Dialkylthionophosphor-saeurechloriden |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US2961456A (enrdf_load_stackoverflow) |
| BE (1) | BE585152A (enrdf_load_stackoverflow) |
| CA (1) | CA630676A (enrdf_load_stackoverflow) |
| CH (1) | CH377793A (enrdf_load_stackoverflow) |
| DE (1) | DE1104501B (enrdf_load_stackoverflow) |
| FR (1) | FR1243590A (enrdf_load_stackoverflow) |
| GB (1) | GB887689A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1183493B (de) * | 1960-11-07 | 1964-12-17 | Bombrini Parodi Delfino Societ | Verfahren zur Herstellung von O, O-Dimethylthiophosphorsaeurechlorid |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2692893A (en) * | 1952-04-05 | 1954-10-26 | American Cyandmid Company | Method of preparing dialkyl chlorothiophosphates |
| US2715136A (en) * | 1949-04-29 | 1955-08-09 | Victor Chemical Works | Method of preparing dialkyl thionochlorophosphates |
-
0
- BE BE585152D patent/BE585152A/xx unknown
- CA CA630676A patent/CA630676A/en not_active Expired
-
1958
- 1958-12-02 US US777609A patent/US2961456A/en not_active Expired - Lifetime
-
1959
- 1959-11-30 CH CH8130059A patent/CH377793A/de unknown
- 1959-11-30 GB GB40590/59A patent/GB887689A/en not_active Expired
- 1959-11-30 DE DES66068A patent/DE1104501B/de active Pending
- 1959-12-02 FR FR811892A patent/FR1243590A/fr not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2715136A (en) * | 1949-04-29 | 1955-08-09 | Victor Chemical Works | Method of preparing dialkyl thionochlorophosphates |
| US2692893A (en) * | 1952-04-05 | 1954-10-26 | American Cyandmid Company | Method of preparing dialkyl chlorothiophosphates |
Also Published As
| Publication number | Publication date |
|---|---|
| US2961456A (en) | 1960-11-22 |
| BE585152A (enrdf_load_stackoverflow) | |
| CH377793A (de) | 1964-05-31 |
| FR1243590A (fr) | 1960-10-14 |
| GB887689A (en) | 1962-01-24 |
| CA630676A (en) | 1961-11-07 |
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